How To Play Match-Maker
by Skylight369
Summary: Hiccup and Astrid always say that they are just friends, although it is clear that both of them want more. So Hicca and Raeda decides play cupids.
1. Operation Hiccstrid

**A/N: Hey guys! Skylight here with a new story! This is going to be my first modern day au fic. Hope you guys like it! Read and review.**

**Disclaimer: I do not own anything from How to train your dragon.**

**Chapter 1: Operation Hiccstrid**

The sound of the room door opening made Hicca Haddock look up from her biology book and see her twin brother, Hiccup Haddock, walk in with his eyes on the screen of his cell phone. She watched as her brother stumbled a bit, being too focused on whatever was on the screen, before he reached his bed on the opposite side of the room. Seeing the bright smile on her brothers' face, Hicca immediately knew the reason behind it.

"You're texting Astrid again, aren't you?" She asked although she knew the answer well.

"Yes, how did you know?" Hiccup asked, not looking up from his phone.

"Lucky guess." Hicca said sarcastically, although her brother didn't pick up on the sarcasm like he usually does. "Any chance you're going to ask her out?" Again, she already knew the answer to that question and it frustrated her every time she heard it.

Hiccup finally looked up from his phone. "No, I told you. Astrid and I are just friends. We're not going to date now or anytime soon. She doesn't like me that way." He then turned his attention back to his phone.

Giving a frustrated sigh, Hicca closed her book and walked out the room. She decided to pay a visit to her and Hiccups' best friend, Raeda Henderson, who lived right next door to their house.

Raeda, Hiccup and Hicca were childhood friends. They always hung out with each other every day since elementary school. The twins' dad, Stoick, and Raedas' parents, Helga and Thaddeus, work in the same electronics company. The adults usually work until late at night so during those nights their children always have dinner and sleepovers together.

Hicca brought out the key to the Henderson household and opened the door, making a beeline to Raedas' room.

Inside, the fifteen year old raven haired girl was painting her walls a different design again, which was not unusual for Hiccup and Hicca. Raeda repaints her walls every four months, unless she gets a sudden inspiration.

Raeda looked up and saw one of her best friends walking inside her room. "Hey Hicca, what's up?" Raeda asked, while painting her wall.

"Trying to keep myself from murdering my brother." Hicca grumbled as she sat on Raedas' bed.

"Uh oh, what did Hiccup do know?"

"He's being completely oblivious, again! He is texting Astrid as we speak and he has that love-struck look in his eyes as always, yet he still adamant about their supposed 'just friends'! It is so annoying!"

Raeda took a break from her painting and looked at Hicca. "I know what you mean. Every time I see Astrid, she always asks about Hiccup and subtly asks whether he has a crush on anyone or not. I try to tell her to go talk to him and be honest about how she feels but always refuses, saying that they're just friends and that he doesn't like her that way."

"I know that's exactly what Hiccup keeps telling me every time I try to encourage him to ask her out. He even said that now when I brought it up again."

Raeda sighed. "Who knew two bright teens could act so dumb."

"They are the perfect match and the sad thing is neither of them knows that." Hicca ranted. "It is faster to watch glaciers move. I say we do something about it, otherwise they are both going to graduate high school as 'just friends'."

Raeda thought about it for a moment and then her eyes sparkled as an idea came to mind. "You're right, we should step in. We gave them plenty of chances to do this on their own. They clearly need help. So we have three options." She then stood up. "Option one: we can strangle them both, option two: we can literally knock some sense into them, using books."

"Both options are tempting." Hicca said. "What's option three?"

Raedas' had a mischievous look on her face. "Option three is the most fun for us." She explained. "I like to call it Operation: Hiccstrid."


	2. Let The Jealousy Begin

**Disclaimer: I do not own How to train your dragon**

**Chapter 2: Let The Jealousy Begin**

The next day, Hicca got up earlier than usual (which for her is really, really early) and walked to Berk High, which was five minutes away from her house. She already left a note for Hiccup, telling him that she left early to check out a book from the library.

So, here she was standing in the parking lot of her school looking for someone, until her eyes landed on a familiar blonde girl.

"Hey, Astrid." Hicca said, walking up to her friend.

Astrid looked and saw the auburn-haired girl walking up to her. "Hey Hicca, where's your brother?"

'Of course she would ask for him.' Hicca thought before answering her. "I came by myself today. I wanted to check out a book in the library and Hiccup takes too long to wake up and get ready. He'll be here anytime soon." She then smirked. "Any reason _that's_ the first thing you ask me?"

"N-no reason." Astrid said, trying not to blush. "Just wondering because you two usually seem to be joined to the hip."

"Right." Hicca said doubtful. "Are you sure it's not because of a crush?"

"Hicca, I don't have a crush on him. We're just friends, best friends." Astrid said defensively.

If Hicca heard the term 'just friends' one more time she would punch someone or something, depending on who or what is closer. "Sorry Astrid. How silly of me to think that you would have a crush on someone you consider your brother."

Astrids' eyes widened at that. "I don't consider Hiccup my brother! Why would you even think that?"

Hicca just gave her an innocent look. "Sorry, Astrid. But you said it yourself , you consider Hiccup as your best friend. So does Raeda. She thinks of him as her brother because of that. I thought you would too. I didn't think you would have a problem with that, though. There is nothing wrong with having Hiccup as a brother and this is coming from his twin."

Astrid thought about it for a moment. She has been trying to convince herself more than anyone else that Hiccup is only her best friend and nothing more. Yet, she just can't accept the fact the he is like her brother. But that doesn't mean she likes him, does it? And even if she did, it wouldn't matter because Hiccup doesn't like her back, does he?

Hicca looked in the distance and smiled. 'It's show time.' She then spoke up, breaking Astrid from her thoughts. "Speaking of whom."

Astrid turned to where Hicca was looking and saw her twin walking towards them.

_Holding Raedas' hand._

Hiccup saw the note his sister left for him and shrugged. It wasn't unusual for his sister to sometimes go to school without him. So he just walked to school with Raeda and the two talked about sketches on the way there. When they reached the parking lot, Hiccup looked around to see if he can find Hicca. Raeda found her and took Hiccups' hand to make him walk in that direction. He didn't really think much about it. He and Hicca knew Raeda since childhood; she is like their older sister. Holding her hand didn't mean anything to either of them.

Too bad no one told Astrid that.

The blonde girl glared at the two hand holders as they walked towards them. 'She thinks of him as a brother, huh?'

"Hey guys!" Raeda said as she and Hiccup reached them. She turned to Hicca. "I hope you got that book you ditched us for."

"I wish." Hicca said. "Fishlegs said that there would be a new botany book in the library, but I think he beat me to it."

"Should have got it yesterday, sis, instead of giving up good sleep." Hiccup said.

Astrid said nothing as she was bothered by the fact that Hiccup and Raeda were _still_ holding hands. She had a sudden urge to shove Raeda as far away as possible.

Fed up, Astrid took Hiccups' other arm. "Come on, Hiccup. Let's go or we are going to be late for class." Before Hiccup could say anything, Astrid pulled him along to their school while Raeda and Hicca watch them leave.

"Do you think we should have told her that there are ten minutes until school starts?" Raeda asked.

Hicca shrugged. "She'll figure it out eventually."

The two shared a knowing look. So far so good.

**A/N: What do you think? Love it? Hate it? Let me know if this needs something more.**


	3. The Bangs

**Disclaimer: I do not own any element from How to train your dragon.**

**Chapter 3: The Bangs**

Finally, to every student's relief, lunchtime came and the cafeteria became flooded with kids within minutes after the bell rang.

Raeda was already sitting on her usual table. She knew that Hicca would delay Astrid for a few minutes so she was looking around for Hiccup. The male Haddock brought his tray full of food and took a seat next to her.

The raven haired girl smiled at him and turned her attention to the entrance of the cafeteria, while Hiccup started eating his food. She saw Hicca and Astrid coming in and, unbeknownst to Astrid, Hicca gave a small hand signal to Raeda, who saw it.

Raeda nodded and turned her attention back to Hiccup. One thing she noticed was that his bangs were reaching his eyes. 'Perfect for Part Two of Operation Hiccstrid' She thought before she spoke up. "Hiccup, when was the last time you cut your hair?"

Hiccup looked up to her in confusion. "Why?"

"'Why?'" Raeda mimicked. "Look at your bangs! I'm surprised you can see clearly through that hair."

Hiccup looked up at his bangs moved it to the right his hand. "I guess I could go for a trim."

"How about a new hairstyle?" Raeda mused. Using her hand, she pushed Hiccups' bangs back, revealing his forehead. "You can get rid of the bang and spike your hair up. That would be a really nice look don't you think? A less dopey look." Hiccup rolled his eyes and playfully swatted her hand away. "Who knows? Astrid might be into the new look." Raeda said with a wink.

That comment made Hiccup blush, as he struggle to get a sentence. "I-I have absolutely n-no idea what you're talking about, Rae." He said shyly. Raeda just giggled.

Just a few tables behind them, Astrid was in the cafeteria line with Hicca getting her food. Astrid saw the exchange between the two and suddenly wanted to tear Raedas' hand off when she saw it running through Hiccups' hair. She narrowed her eyes when she saw Hiccup blushing and looking nervous after Raeda winked at him. 'Why would he be like that if they are having a casual conversation? Unless Raeda is flirting with him. But she's not, is she? There's no way Hiccup likes her in that way, right?' She didn't know for sure since she couldn't hear their conversation, so she was just left with nothing but assumptions.

Hicca, who was behind Astrid in the line, broke her out of her thoughts. "Astrid, will you hurry up? Some of us are starving here." She said. A few kids who were behind her were nodding in agreement. Reluctantly, Astrid tore her gaze from the two sitting at the table and went back to getting food on her plate.

"Does Raeda like Hiccup?" Astrid blurted.

"Of course she does, why wouldn't she? He's one of her best friends." Hicca answered pretending to misunderstand her question.

"No, I mean does she have a crush on him or something?"

Hicca shrugged. "I don't know. Those two are getting closer these days, for all we know; she might have developed a crush on him. Why are you asking?"

"Just wondering." Astrid mumbled, grabbing some a plate full of grapes.

As she moved along the line, Astrid couldn't help but think about what she just saw. Is Raeda flirting with Hiccup? It look like it when she ran her hand through his hand and winked at him. Why else would Hiccup blush? Why was she so bothered if Raeda was flirting with Hiccup? It wasn't like Hiccup was her boyfriend. That thought made Astrids' heart speed up, much to her confusion. She thought back to what Hicca said about considering Hiccup as her brother. The thought was just repulsive to her, though it wasn't because there was anything wrong with Hiccup. Yet, she didn't seem to mind considering him her boyfriend. Why is that?

She looked back at where Hiccup and Raeda were sitting and saw Hiccup laughing at something Raeda said. It made her frown. Was she...jealous? All she knew was that she needed to get to that table quick.

She already got her food and was waiting for Hicca to finish getting hers. "Speed it up, Hicca! This shouldn't take you that long!"

"Calm down, Astrid. What's the rush?" Hicca said, although she knew _exactly_ why Astrid was rushing her. "Honestly, first you hold up the line now you're rushing me. Make up your mind."

Astrid just rolled her eyes and walked ahead, oblivious to the mischievous smile Hicca had one her face. As the two of them got closer to the table, Hicca gave a thumbs-up to Raeda, behind Astrids' back. Luckily, the Henderson girl was the only one who saw it and gave a small nod in reply before she greeted Astrid and Hicca.

**A/N: What do you think of jealous Astrid? Sorry if this is a bit too short.**


	4. The Dance

**Disclaimer: I do not own How to train your dragon**

**Chapter 4: The Dance**

"Hiccup, I have a problem." Raeda said, coming into Hiccup and Hiccas' room.

Hiccup looked up at his best friend. "What's the problem, Rae? You seemed fine on the way back from school and that was about an hour ago."

"Well, you know that school play we are having, Midnight Love? (A/N: I just went with the first name that came to my mind :P)" Hiccup nodded. "Well I'm auditioning for the female lead."

"Wait you're auditioning for a role?" It was Raedas' turn to nod. "Not that I think you're a bad actress Rae, but don't you usually prefer to paint the background scenes for these plays?"

"Well, you can thank you're lovely sister for this." Raeda said sarcastically. "She dared me to do this."

"Ah." Hiccup said in understanding, being the receiver of his twins' many dares.

"Anyways." Raeda said continuing. "The auditions are tomorrow and I was just going over the script, and there's a dance scene, a _slow _dance scene and I'm not prepared. I was hoping that maybe you would help me with that."

Hiccup immediately understood what Raeda was asking and was hesitant. It wasn't because there was anything wrong with dancing with Raeda, especially if it was just for practice; it was because he was unsure about his own ability to dance. He has never slow dance with any girl before, although he was hoping that would be changed by a certain blonde girl.

"Uh Rae, I'm not sure if I am the best guy to come to for this. I haven't slow dance ever before and I can't guarantee that I won't step on your feet a few times."

"You're fairly co-ordinated Hiccup and you're like the only guy I am comfortable with going to for this." When she saw Hiccup reluctant expression, she became more persuasive. "Pretty please Hiccup? The audition is tomorrow and they will ask us to do this scene. Please help me get through your evil twins' dare." She pleaded with her puppy dog eyes.

Hiccup sighed. He was amazed at the fact that his best friend can have both a cute puppy-dog stare and an intense, murderous glare. Something told him that if he didn't say yes, he would get the latter of the two looks.

"Fine." He conceded.

"Thank you, Hiccup!" Raeda said happily. She gave him a quick hug before taking her iPod and plugging it on the twins' speakers.

'Well, on the bright side.' Hiccup thought. 'If I ever somehow take Astrid to one of our school dances, then I can have the confidence to slow dance with her.' The thought made him smile, until Raeda broke him out of his thoughts. It was time to start practicing.

Astrid walked to the Haddock household, wanting to get her book which Hicca borrowed. The auburn-haired girl was supposed to return it to her in school, but she seemed to have forgotten and told Astrid to get it from her house. Luckily for Astrid, the house was in the path between school and her own house.

On her way there, Astrid couldn't help but think about Hiccup. They've both been really good friends for years. It's supposed to be like that, right? Nothing more than friendship. Then why did Astrids' heart clench when she saw Hiccup and Raeda talking. It's not like they haven't done it before? But Raeda has never held his hand before, nor has she ever touched his hair or made him blush or wink at him. Could Hicca actually be right? Did Raeda realised she had feelings for Hiccup and has started acting on them. Will Hiccup reciprocate these feelings?

'Why does it bother me so much?' Astrid thought. Why does it matter to her so much? 'Neither Raeda nor Hiccup was in a relationship. They were free to date each other if they wanted.' For some reason, that did not help Astrid at all. She reached the steps of the Haddock house when she decided to talk to Hiccup after she gets her book back from his twin.

She rang the bell and a few minutes later, Hicca answered with a smile. "Hey Astrid! Here for your book or Hiccup?" She asked with a smirk.

_Both_ "The book." Astrid said.

Hicca allowed her in and lead her upstairs to the study, which was across hers' and Hiccups' room. "Wait here, I just need to find the book." She said, before going into the study. Astrid stood there for a moment before looking at the room across. She decided to walk towards it, but paused when she heard music being played inside. Curious, she slowly opened the door and she was not expecting to see what was inside.

_Hiccup and Raeda slow-dancing to a romantic song_

Suddenly, Astrids' blood was starting to boil. 'How dare her! Dancing with him! He's mine!' The anger disappeared as Astrid eyes widened when she realised what she had just thought. She slowly closed the door as a realisation came to her.

"Here you go." Hiccas' voice snapped Astrid out of her thoughts. She handed her the book, which Astrid took while trying to regain her composure. "You okay?"

"Yeah, sure. Why wouldn't I be?" Astrid said, trying to sound casual.

Hicca shrugged. "Want me to let my brother know you're here?"

"No, don't. He's clearly busy right now." Astrid said bitterly, staring at the door. She went downstairs and left. Outside, she took a deep breath before she thought about her realisation. She likes Hiccup. Maybe even more than that, maybe even love. Why hadn't she seen that before? What was there _not_ to like, or love, about Hiccup? He has a cute and dopey look with an equally cute and dopey smile. He is smart, but not overly smart like Fishlegs. His sarcasms always make her smile. He not like the other guys in her high school. Astrid wanted to slap herself. She liked him this whole time and now there's a chance she could lose him to Raeda. 'No, you don't know that. Neither of them had said anything, yet. It might not be too late.' She needed to talk to both of them tomorrow no matter what.

As soon as she saw Astrid out the door, Hicca immediately went to hers' and her brothers' room and opened the door. She watched Hiccup and Raeda slow dance for a moment before speaking up. "You both are really good."

Taken by surprise, Hiccup stopped and immediately saw who that voice belonged to. "Oh hey, sis. Thanks."

"You should both audition for the lead roles." Hicca suggested.

"No thanks, sis. I can't act." Hiccup said. "I'm going to get some water, do you want some Rae?"

"Nope, I'm good. Thanks." Raeda answered. Hiccup left the room and Hicca immediately made sure he left before she joined Raeda on the bed.

"So did Shield-maiden (Astrid) come by?" Raeda asked. The two girls agreed to discuss their plan in code, just in case Hiccup overhears them talking.

"She did and she is probably coming up with a book filled with ways to murder Artist (Raeda)." Hicca answered. "Artist and Healers' (Hicca) plan is soaring sky high."

"By the way, I was wondering, should Artist and Healer help Blacksmith (Hiccup) with his feelings for Shield-maiden?"

"No need, Blacksmith is already aware and is just shy about it." Hicca said.

Raeda smiled. "This is way better than the April Fool's prank of 2009."

"I don't know about that, Rae. I still laugh every time I see the video of it." Hicca said. She then whispered in case her brother was outside the door. "But maybe we both should audition for that play. We're both pretty good at acting."


	5. The Date

**A/N: Here we go. Two stories updated at once. Hope you guys like both. Please read and review.**

**Disclaimer: I do not own anything from How to train your dragon**

**Chapter 5: The Date**

The next morning, Astrid went to the school courtyard looking for someone. As soon as she set her eyes on a raven-haired girl, she immediately went towards her.

"What is going on?" She demanded.

Raeda simply looked up and stared at Astrid. "Hello to you too, Astrid. I'm fine, how have you been?" She asked innocently.

"Are you and Hiccup dating?" Astrid pressed.

"Are Hiccup and I dating?" Raeda repeated. "You seem really bothered by that thought, why? I mean it's not like Hiccup is cheating on you or anything since he is not even your boyfriend."

"I know that." Astrid said, clenching her jaws. 'Though I really want him to be.'

"Are you jealous, Astrid?" Raeda smirked.

"I'm not jealous!" Astrid hissed.

Just then Hicca walked towards the two girls, seemingly oblivious to the exchange.

"Hey, guys!" She greeted before turning to Raeda. "Rae, I'm not going to be there for dinner tonight, because I am going to go to the library to finish up my science project due tomorrow."

"Oh, that's okay. I can just have dinner with Hiccup." Raeda said, while looking at Astrid who was starting to listen in. "It will just be me and him having dinner together and maybe we can watch a movie afterwards. I'm kind of in the mood for a _romance_ movie."

That was all Astrid heard before she stormed off into the school, missing the fist-bump exchange between the two girls she left behind.

She immediately went to look for Hiccup and found him by his locker. "Hiccup, I need to talk to you." She said.

"Can it wait? Class is going to start in a few minutes and I don't want to be late." He said as he closed his locker.

Instead of responding, Astrid just pulled him into an empty classroom, ignoring his protests, and locked the door.

"Astrid, what is it with you?" Hiccup asked, taken by surprise.

"What is it with me?" Astrid asked incredulously. Her patience has completely run out. "What is with you? You hold hands with Raeda! She strokes your hair and winks at you and you blush in return! You slow-danced with her!"

"How did you know about-?"

"Are you dating Raeda? Do you want to date her? Does she want to date you? Just answer the questions!" Astrid demanded.

"Astrid, calm down." Hiccup said, wondering what's going on with her. "You are starting to sound jealous."

"Of course, I'm jealous you idiot! I'm jealous of her!" Astrid blurted in anger.

That got Hiccup surprised and confused. "W-what?"

Astrid took a deep breath and calmed down before speaking up. "I like you Hiccup. I have for awhile. I like your adorable smile, your witty, humorous sarcasm, I like everything about you. I got jealous when I saw you with Raeda. I don't want to think of you dating her and I do not want to think of you as just a friend. So yes, I am jealous of Raeda."

Hiccup just stared at Astrid as he let the words sink in. He took a deep breath before saying. "Y-you like me?"

Astrid nodded.

"W-wow." Hiccup said. "If I had known that, I would have asked you out a long time ago."

"R-really?" Astrid asked, it was her turn to be surprised.

Hiccup nodded. "Astrid, Raeda is just my childhood friend. She is more like an older sister to me and Hicca. And even if she wasn't, I would like her in _that_ sense because I already like you. You're beautiful, smart, and fierce. I've been having a crush on you since I first met you. I-I didn't think you would like me back."

"Really?"

"Really."

"So what are you doing tonight?" Astrid asked coyly.

Hiccup caught on. "Going on a movie date with you." He answered.

Astrid smiled. "Pick me up at eight." She said before they walked to the door. When they reached the door, Hiccup gave Astrid a kiss to the cheek. "It's a date." He said before he unlocked the door and left. Astrid just stood there, dazed at what happened before she left the classroom with a big smile on her face.

Hiccup saw his sister and Raeda talking and walked up to them. "Hey, sis, Rae. I am not going to be home for dinner. Astrid and I are going to the movies."

"Let me guess." Hicca said, leaning against the locker. "Another 'just friends' hang out."

"Actually, this one is a date." Hiccup said sheepishly.

"Really?" Raeda asked. Hiccup nodded. "Well about time. What made you two realise that?"

"Well, apparently Astrid thought you were flirting with me."

"She did?" Raeda asked, raising her eyebrows. "Hmm, I wonder what gave her that impression." She and Hicca exchange knowing looks which went unnoticed by Hiccup.

"Well, I have to go to class. See you two later." As soon as he left, Raeda and Hicca exchanged a high-five.

"Finally. I thought they were never going to go out." Hicca said smiling as they walked to class.

"I know, I thought I would have to imply to Astrid that I went on a date with Hiccup before she went to him." Raeda said.

"We're definitely going to order pizza to celebrate the victory of Operation: Hiccstrid, tonight." Hicca said happily and Raeda nodded in agreement. They stopped when they saw their friend, Fishlegs Ingerman, nervously approached their other friend, Ruffnut Thorston who was talking to her twin, Tuffnut.

"H-hey Ruffnut." Fishlegs said nervously.

Ruffnut shoved her twin aside and turned to face Fishlegs. "Hey, Fish. What's up?" She asked with a hint of hope in her expression.

Fishlegs became more nervous that he started stammering. "W-well, you s-see. I was wondering I-if well m-m-maybe if you weren't busy t-then-" He was then cut off by the sound of the bell. "Oh, there goes the bell. I have to go. Don't want to be late. Bye!" Before Ruffnut could say anything, he scurried off red in the face. He missed the disappointed look in Ruffnuts' face before the blonde girl went to join her brother.

Having seen and heard the entire thing, Hicca and Raeda turned to each other. Both had the same thought in mind.

"Operation: Rufflegs?"

"Operation: Rufflegs."

**A/N: And here we are. Operation: Hiccstrid was a complete success. Hicca and Raeda seemed to have found a new job as match-makers :). I am thinking of doing something different. Remember in the previous chapter it was mentioned that Hicca and Raeda pulled an April Fools prank in 2009? Well I was thinking about it and I decided to put that as a prompt for anyone who is interested in writing a side story for that. You can title it whatever you want and you can use my OC characters. But keep in mind, you can only use my OC characters in 'the April Fools prank' storyline and not anything else. If you want to write a story on this prompt, PM me and let me know I would love to read it. Those who do will get a special shout-out in my 'Riders of Berk' series.**


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